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Vacation rentals in Berwyn

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Quick stats about vacation rentals in Berwyn

  • Total vacation rentals

    Explore 110 vacation rentals in Berwyn

  • Nightly prices starting at

    Berwyn vacation rentals start at ﺩ.ﺇ 73 per night before taxes and fees

  • Verified guest reviews

    Over 7,970 verified reviews to help you choose

  • Family-friendly vacation rentals

    60 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    110 of Berwyn vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace across Berwyn rentals

  • 4.8 Average rating

    Berwyn stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated vacation rentals in Berwyn

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
A living room is presented with light-colored walls and hardwood flooring. Comfortable seating arrangements include two light armchairs and a grey sofa with decorative pillows. A round coffee table sits in the center, complemented by a chic area rug. Natural light enters through two windows, enhancing the bright atmosphere.
Apartment in Berwyn
4.83 out of 5 average rating, 111 reviews

House to Relax

Elegant/Spacious 2bd Apt close to Chicago Stay includes: * 1 Free Street Parking (1 parking pass per night provided by host) * Garage parking available for small SUVs and compact vehicles only (trucks and other vehicles must use street parking) *Free Wi-Fi *Comfortable Queen Bd *50' smart TV with all streaming services for you to sign in and enjoy your favorites *Fully Stocked Kitchen + Microwave + Fridge + Coffee/Tea maker The space 5-10min walk > lots of restaurants/Local Gambling Slots 10min drive > Mall/Oak Park/Hospitals/Brookfield Zoo 20min drive> Medical District/Medicine/Doctors 25min drive> Ohare & Midway airport/Northwestern/Rivers-Bally Casino/Downtown Chicago/Golfing

Guest favorite
The kitchenette area includes a stainless steel refrigerator, a microwave, and a Kuerig coffee maker on a pull-out countertop. Below are white cabinets providing storage space, with the upper wall featuring light switches and an electrical outlet.
Guest suite in Berwyn
4.85 out of 5 average rating, 149 reviews

Best Place to Rest, near Chicago

Unit with private entrance, close to Berwyn's restaurants, bars, shops, and entertainment. Close to public transportation via the Metra Train Station, Pace Buses, and near the CTA Pink [1.5 miles], Blue [2.3 miles], and Green [3.4 miles] Train lines. Near Oak Park, North Riverside, and Chicago. This is an awesome location. There is parking on the street (A street pass is required and will be provided each day). The unit is 185 sq ft located in the basement with 4 stairs, ceiling height is 6' 6"

Superhost
A modern living area features a sleek black sofa paired with two cozy white armchairs. Natural light pours in through large windows adorned with light grey curtains. Minimalist decor includes two framed artworks and a small wooden side table that complements the space.
Apartment in Berwyn
4.85 out of 5 average rating, 167 reviews

2 bedroom• 3 beds • 1 bath Apartment in Berwyn

Enjoy a stylish and elegant experience at this centrally-located private apartment On famous Route 66. Sunny, clutter free very spacious 2nd floor. Apt. Can sleep upto 6 ppl. Inflatable bed added for extra sleep option. Prepped for photo sessions of your own. •Restaurants, Auto repair shops and Walgreens are walking distance and much more. •Metra is a 10-15 minute walk. •DT Chicago 18 min •Brookfield Zoo 15 min Away •Midway Airport 15 min •O’Hare Airport 30 min •Mall 10 min •Loyola Hospital

Guest favorite
Home in Berwyn
4.82 out of 5 average rating, 49 reviews

Cozy & Peaceful Oasis Near City | 2BR + 1.5 Bath |

Unwind in this stylish 2-bedroom home in Berwyn just 20 mins from Downtown Chicago and Midway Airport. Berwyn is full of award-winning restaurants, bars, shops, & attractions. Adventure through Chicago from this prime location with ample street parking, accessible highways, and public transportation. Enjoy the private backyard during the summer months, relax on the hammock, and even grill a delicious meal! • Full Kitchen • 2 Bedrooms • Private Backyard • High-Speed Wi-Fi • Pool Table • 2 Levels

Top guest favorite
A light-filled living area features a soft blue couch and armchairs, complemented by a decorative rug. Art pieces on the wall offer a subtle touch of color. An adjacent dining area is visible, with a wooden table surrounded by chairs.
Home in Berwyn
4.94 out of 5 average rating, 70 reviews

Berwyn Beauty

Don't miss out on this charming home away from home! Including 3BD/2BA with a finished basement, our house sits in the heart of the Depot District of Berwyn. It is stocked with all the amenities you will need for your stay, including laundry facilities in the basement. A beautiful backyard awaits you to enjoy the outdoors! There is a two-car garage for easy parking, and the Metra train is steps away for a quick trip to downtown Chicago! The area has a variety of restaurants, bars, & breweries!

Superhost
A cozy living area is highlighted by two armchairs in warm tones, positioned beside a stylish blue sideboard. A large flat-screen TV is mounted on the wall, and a decorative bowl sits atop the sideboard. Soft lighting is provided by a standing lamp, enhancing the inviting atmosphere.
Apartment in Berwyn
4.78 out of 5 average rating, 51 reviews

Contemporary NEW Entire Suite Berwyn/Riverside

Welcome to your private oasis! This beautifully NEW appointed 1 bd unit offers the perfect blend of modern convenience and contemporary style. Whether you’re here for a weekend getaway or an extended stay, this contemporary retreat is your perfect home base. Explore the vibrant attractions of Berwyn or the excitement of Chicago, just a short trip away. Book today to secure your stay and experience the blend of comfort and style in this chic contemporary gem. We look forward to hosting you!

Superhost
A spacious bedroom is furnished with a large bed featuring a gray and white patterned blanket. Art pieces are displayed on the wall above the bed, and two bedside lamps with warm light sit on either side. A bold, geometric area rug adds texture to the space.
Guesthouse in Oak Park
4.91 out of 5 average rating, 268 reviews

Gallery Loft of Oak Park #1 Top Host in IL

Gallery Loft of Oak Park <a href="https://news.airbnb.com/the-number-one-new-host-in-each-us-state/">2021 #1 Top Host in Illinois</a> is a Chicagoland gem near the birthplace of Ernest Hemingway, Frank Lloyd Wright Home/Studio. 2nd story flat furnished in vintage mcm style, featuring local artists. Walking distance to live music (Fitzgerald's, Friendly Music Community), and restaurants. Firepit access, easy street parking and kitchen well stocked. Private porch. Perfect long/short term stays.

Top guest favorite
A bright kitchen area features a round table with a red and white checkered tablecloth and four white chairs. A small sink and a gas stove are present, along with a refrigerator. Natural light filters through a window adorned with a red gingham curtain.
Apartment in Berwyn
4.92 out of 5 average rating, 529 reviews

Private apartment with retro vibe

Cozy 1 BR apartment with retro touches in Berwyn a block from Oak Park. 2nd floor private apartment. Wifi, cable, premium channels. Full kitchen. Queen bed plus twin sofa bed, + 2 twins available on request. EASY free street parking right by unit. Quick drive to City. Convenient to both airports, United Center and walk to Fitzgerald’s Club. Near Blue Line, restaurants, great bakery. NO smoking, candles or glitter! (Yes, I truly needed to add the “no glitter” rule! (You can only imagine!)

Guest favorite
A living room features a mid-century velvet sofa in a rich green hue, paired with a tan leather chair. Natural light streams through large windows, illuminating a glass coffee table and a decorative wall with layered wooden frames. The original brick fireplace adds character to the space.
Home in Berwyn
4.97 out of 5 average rating, 228 reviews

RetroModern Bungalow | free parking | pet friendly

Experience the city in style at our Retro Modern Bungalow, the perfect pad for up to four friends. Featuring two spacious bedrooms—each with a king bed and luxury linens—a propane fire pit and a pup-friendly, fenced-in backyard. With central HVAC, speedy WiFi, a dedicated workspace, and a pack-n-play crib available at no cost. Central location—just south of Oak Park, 15 mins from Midway airport, and 20 mins from downtown. Park for free in our garage and catch the train a few blocks away.

Top guest favorite
The exterior of a modern three-story bungalow is showcased, featuring a mix of brick and dark paneling. A neatly landscaped front yard includes a path leading to the entryway, flanked by lush greenery and decorative stones. The structure retains a contemporary architectural style.
Home in Berwyn
4.97 out of 5 average rating, 37 reviews

The Architectural Haven

Welcome to The Architectural Haven! Enjoy comfort and luxury in our modern Berwyn bungalow, a serene escape only 15 minutes from downtown Chicago. Nestled in a charming neighborhood, this secluded retreat offers the perfect place to relax and recharge. Our thoughtfully designed space is fully equipped with premium amenities and unique architectural touches. Every room invites you to feel at home, ensuring a memorable stay you’ll want to revisit We look forward to hosting you!

Guest favorite
A vibrant cityscape of downtown Chicago is captured at dusk, showcasing towering buildings including the Willis Tower. The scene is highlighted by a bridge over a river, with colorful hues in the sky reflecting pink and purple tones.
Home in Berwyn
4.9 out of 5 average rating, 157 reviews

Beautiful Bungalow, Near Downtown Chicago

Beautiful, cozy, vintage home in a centrally located quiet neighborhood. Close to downtown Chicago, O'Hare and Midway Airports as well as many attractions, museums and great places to eat. This home includes High Speed Wifi, Full Kitchen, Full washer/dryer, tv's with streaming and a game loft full of board games and game consoles for all guests to enjoy. Contactless check-in and check-out with keyless entry. 3 Bedrooms, 4 queen beds, 1.5 baths. Sleeps 8 guests total.

Guest favorite
A well-lit sleeping area features a spacious bed adorned with patterned linens and accent pillows. A wooden nightstand holds a lamp. A clothes rack stands nearby, alongside a chair with a throw pillow. Dark curtains frame a window, adding privacy to the room.
Apartment in Oak Park
4.83 out of 5 average rating, 111 reviews

Bright Boho Haven free parking

Welcome to our bright, newly constructed 1-bedroom, 1-bath Airbnb in the heart of Oak Park. Enjoy a sunny, modern space with a beautiful bathroom, free parking, and all the essentials. Just steps from grocery stores, coffee shops, and the Oak Park Blue Line stop—reach downtown Chicago in under 30 minutes. Perfect for a cozy getaway or work trip, with fast Wi-Fi, smart TV, kitchenette (no oven!) and a peaceful, walkable neighborhood. We can’t wait to host you!

Popular amenities for Berwyn places to stay

GymBBQ grillLaptop-friendly workspaceWifiAir conditioning

Stay near Berwyn's top sights

Fitzgerald's

93 locals recommend

Oak Park Conservatory

58 locals recommend

Kinslahger Brewing Company

20 locals recommend

Other great vacation rentals in Berwyn

Guest favorite
Home in Berwyn
4.92 out of 5 average rating, 38 reviews

Paradise in the Park

Superhost
Apartment in Berwyn
4.89 out of 5 average rating, 9 reviews

Spacious 2BR Oasis;nearChicago/OakPark/near train

Top guest favorite
A cozy living room arrangement is showcased, featuring a comfortable sectional sofa with decorative pillows and an accent chair. Large windows adorned with elegant curtains allow natural light, with colorful stained glass adding character. A round coffee table sits centrally on a patterned rug.
Home in Berwyn
5.0 out of 5 average rating, 23 reviews

Chic Bungalow Near Chicago - Stained Glass Gem

Top guest favorite
Apartment in Berwyn
4.91 out of 5 average rating, 76 reviews

Cozy, Sunny, and Clean Apt 3 bd Free Parking

Guest favorite
Apartment in Berwyn
5.0 out of 5 average rating, 13 reviews

4 King Beds + Parking | 20 Min Train to Chicago

Top guest favorite
Apartment in Berwyn
5.0 out of 5 average rating, 15 reviews

A cosy apartment 20 min by car from Chicago

Guest favorite
A cozy living room features four plush purple chairs arranged around a circular table. A modern television is mounted above a white brick fireplace, complemented by bookshelves filled with various items. A large potted plant adds a touch of greenery, enhancing the warm atmosphere.
Home in Oak Park
4.88 out of 5 average rating, 100 reviews

A Comfortable Stay While You are Away in Oak Park

Guest favorite
Apartment in Berwyn
4.86 out of 5 average rating, 7 reviews

Home Theater Retreat w/ 65” TV + Surround

When is the best time to visit Berwyn?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ 323ﺩ.ﺇ 345ﺩ.ﺇ 367ﺩ.ﺇ 382ﺩ.ﺇ 496ﺩ.ﺇ 606ﺩ.ﺇ 470ﺩ.ﺇ 444ﺩ.ﺇ 404ﺩ.ﺇ 393ﺩ.ﺇ 360ﺩ.ﺇ 367
Avg. temp-3°C-1°C4°C10°C16°C22°C25°C24°C20°C13°C6°C0°C

Frequently Asked Questions

  • What are the best places to stay in Berwyn?

    Berwyn has family homes, cozy bungalows, and apartments suited for groups, solo travelers, and families. Staying near the Depot District can make it easy to explore local dining and shops in a vibrant neighborhood.

  • What are the best things to do in Berwyn with kids?

    Families often enjoy playful afternoons at community parks, visiting local libraries for children’s activities, and attending seasonal cultural events around town. Art workshops and family-friendly cafés are also frequently suggested.

  • What are some of the best things to do in Berwyn?

    Explore Berwyn’s Depot District for public art, dining, and shops, and enjoy local parks for outdoor relaxation. The city has vibrant community events and a growing arts scene worth experiencing.

  • How is the weather in Berwyn?

    Berwyn has cold winters around 19–33°F (-7–0°C) and warm summers reaching 68–85°F (20–29°C). Pack layers for spring and autumn, which bring mild temperatures and occasional rain.

  • When is the best time to visit Berwyn?

    Late spring through early autumn is often recommended for mild weather, outdoor activities, and local festivals. Winter is quieter, with chilly temperatures suited for indoor experiences.

  • What are the best places to visit in Berwyn?

    Berwyn has vibrant public murals in the Depot District, community parks for relaxing outdoors, and a variety of galleries that highlight local creativity. The area is known for independent shops, neighborhood coffee spots, and historic architecture throughout the community.

  • What are some hiking trails in Berwyn?

    Berwyn has walking paths in neighborhood parks for leisurely strolls, and wooded trails can be found in nearby forest preserves. Local residents often enjoy exploring these green spaces throughout the year.

  • What are some family activities we can do in Berwyn?

    Explore playgrounds and community centers for hands-on activities, enjoy story hours at the Berwyn Public Library, and visit kid-friendly local eateries. Seasonal events invite families to connect with Berwyn’s welcoming community.

  • What are some of the best day trip ideas from Berwyn?

    Many visitors explore nearby forest preserves for nature walks, visit museums in the surrounding area, or experience the vibrant city life of Chicago. Botanical gardens and historic neighborhoods around Berwyn are frequently suggested.

  • Are there any pet friendly accommodations available in Berwyn?

    Berwyn has pet-friendly stays, especially in residential neighborhoods and private homes. Look for listings that welcome pets and provide easy access to parks for walks.

  • What are some local tips for visiting Berwyn?

    Consider exploring Berwyn on foot to discover public murals and independent shops in the Depot District. Local farmers’ markets and street festivals are a great way to experience the area’s community vibe.

  • What is Berwyn known for?

    Berwyn is known for its historic Route 66 ties, lively Depot District, and a tradition of community events. Public art and mid-century architecture add distinctive character to the city’s landscape.

  • What are the best hidden gems to explore in Berwyn?

    Discover smaller art galleries, quirky vintage shops, and locally owned cafés tucked around the Depot District. The city’s public murals and community theater performances are also frequently suggested for visitors looking for unique experiences.

  • What are the best foods to try in Berwyn?

    Berwyn has locally rooted flavors including classic Chicago-style pizza, diverse Latin American and Eastern European dishes, and casual diners serving community favorites. Bakeries in town are known for sweet pastries and fresh bread.

  • What should I bring for a trip to Berwyn?

    Pack comfortable walking shoes for exploring neighborhoods, layers for variable temperatures, and rain gear in spring and autumn. Having a reusable water bottle and sun protection is also often recommended.

  • What is the nightlife in Berwyn like?

    Berwyn has laid-back lounges, locally owned bars, and venues hosting live bands or community performances. The Depot District is known for its vibrant nightlife scene with casual eateries and music events.

  • What are the most popular events or festivals in Berwyn?

    Berwyn hosts music festivals, art fairs, and community parades, often centered around the Depot District and public parks. Summer block parties and seasonal celebrations draw neighbors and visitors together throughout the year.

  • Are there family friendly vacation rentals in Berwyn?

    Berwyn has vacation rentals suited for families, such as spacious homes and apartments near parks and playgrounds. Many hosts provide amenities like full kitchens and child-friendly spaces to make group stays comfortable.

Destinations to explore